Extra stylish and functional, this relaxed pairing of a grey blazer and a charcoal crew-neck t-shirt brings excellent styling possibilities. Tan suede work boots can immediately play down an all-too-dressy look. We know it's hard to stay on-trend in extreme weather, but this outfit is hard proof that it's quite doable. This getup is a bright example 50-year-old men can still very well draw compliments.